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<h1><a href="https://archiveofourown.org/works/27036985">Pressure Luck</a> by <a class='authorlink' href='https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67'>CS_impala67</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>My Kinktober 2020 fics [15]</td></tr>

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Alternate Universe - College/University, Bottom Castiel (Supernatural), Bottom Castiel/Top Dean Winchester, Fluff and Smut, Friends to Lovers, Getting Together, Kinktober, Kinktober 2020, M/M, Massage, Roommates, Top Dean Winchester</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-10-16</td></tr>

<tr><td><b>Updated:</b></td><td>2020-10-16</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-06 18:15:09</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>2,815</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27036985</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>“Dude. What's your problem?” His roommate called from the other side of the room. Dean had been sitting on his own bed in their shared dorm room, watching a movie on his laptop with his earbuds plugged in. Cas had completely forgotten he was even there; he had been so absorbed in his assignment.</p><p>     “It's just my back and neck.” He grumbled. “Guess I've just been sitting here too long.” He reasoned.</p><p>     “Want me to massage you?” Dean asked, causing Cas to freeze. No way could he have heard him right. His heart was beating fast though, at just the thought of his roommate’s hands on him. Cas had been nursing a steadily growing crush on his Adonis of a roommate, now turned best friend.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester</td></tr>

<tr><td><b>Series:</b></td><td>My Kinktober 2020 fics [15]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1961551</td></tr>

<tr><td><b>Comments:</b></td><td>4</td></tr>

<tr><td><b>Kudos:</b></td><td>148</td></tr>

</table>

<a name="section0001"><h2>Pressure Luck</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>For Kinktober Day 15 I chose Massage</p>
    </blockquote></div><div class="userstuff module">
    
    <p>     Castiel sat at his desk, trying to concentrate on his essay assignment that was due at the end of the week. It was mostly done, he just needed to tweak it a bit, and add in citations. He'd been sitting in his cheap computer chair for hours working on it, and his neck and back were definitely paying the price. He leaned back and twisted his body, trying to work out the kinks he felt, to no avail. He sighed loudly in the quiet room, annoyed at the aches he was feeling.</p><p>     “Dude. What's your problem?” His roommate called from the other side of the room. Dean had been sitting on his own bed in their shared dorm room, watching a movie on his laptop with his earbuds plugged in. Cas had completely forgotten he was even there; he had been so absorbed in his assignment.</p><p>     “It's just my back and neck.” He grumbled. “Guess I've just been sitting here too long.” He reasoned.</p><p>     “Want me to massage you?” Dean asked, causing Cas to freeze. No way could he have heard him right. His heart was beating fast though, at just the thought of his roommate’s hands on him. Cas had been nursing a steadily growing crush on his Adonis of a roommate, now turned best friend.</p><p>     They had been rooming together at college for 3 years now, since they were freshmen. Cas remembered walking into his dorm room on the first day of freshman year, and stopping dead in his tracks as he first laid eyes on Dean, who had been sprawled across his own bed, throwing a football up in the air to himself. His biceps were the first thing Cas noticed, bulging out of a tight black tea. That's when Dean sat up to greet him, and Cas laid eyes on the most gorgeous face he had ever seen in his life. ‘Green. So green.’ He thought, as he gazed into the other boy’s eyes. His gaze slowly made its way down Dean's face as he took in the astounding number of Freckles adorning the Adonis’ face. Lower he continued to look, until he saw an enticing smirk that encased a set of white pearly teeth. A throat-clearing had jolted him out of his head, and his eyes had snapped back up to me Dean’s, amusement clear on the man's face.</p><p>     “Hey I'm Dean.” He had said as he stood up with a hand out to shake Cas’.</p><p>     “Castiel. I'm uh...my name is Castiel.” Cas had managed to stutter, flushed at being assigned to share a room with this Greek god.</p><p>     They had managed to grow really closed in the last 3 years and Cas could easily call Dean his best friend now. Normally, he no longer blushed at any of their interactions, like he had in the beginning. Until now. Now, that he could have sworn he heard Dean asked if he wanted a massage.</p><p>     “Come again?” He squeaked out, voice cracking with nerves.</p><p>     “Do. You. Want. A. Massage?” Dean repeated slowly, as if Cas was stupid. Which, he must be because he still couldn't make sense of Dean's words.</p><p>     “Why…uh…why would you massage me?” He stammered out, confused and unsure.</p><p>     “Dude seriously? I told you weeks ago I'm taking that massage therapy course. I can practice on you. It would help those aches you got and it would give me a chance to practice some of what I'm learning. It's a win-win man.” He beamed excitedly. “Come on, it'll be great! Take your shirt off and go lay in my bed. I'll go grab some lotion from one of the girls down the hall. One of ‘em's gotta have some I can use.” Dean ordered as he walked out of the room, leaving Cas standing there, stunned about what just happened. He eventually shook himself out of his stupor and followed Dean's instructions, still not believing he was about to get a massage from the hands of the man he had a one side of massive crush on.</p><p> </p><p>*********************************************************************************************</p><p> </p><p>     As Dean made his way out of their dorm room, he immediately started mentally berating himself. How Fucking stupid was he? ‘W<em>ant me to massage you</em>?’ Ugh, Fucking idiot! He had no idea what possessed him to throw that out there, like it was just an everyday thing that they did. As soon as he said it, he wished he could take it back. Of course, he did the complete opposite instead, and doubled down with his suggestion. Like he said, Fucking idiot. The only reason he left the room was to give himself a few minutes to get his head on straight. He didn't actually need to borrow lotion from any of the girls, he had some under his bed. Cas didn't need to know that though.</p><p>     Fuck, this is not good. His word vomit was probably going to be responsible for his best kept secret finally being revealed; I.E. his massive crush on his roommate. The crush he has been pushing down for three years now, ever since he met the sexy nerd their first day as freshman. He had just been lying on his bed, tossing the football up and down, till, in walked in the most attractive dude Dean had ever seen. Blue was the first thing he noticed. Cas’ eyes were a captivating, electric blue. The color almost didn't look real. His lips were what Dean had noticed next. They were so full, and soft, and pillowy looking. He couldn't help but imagine how they would feel pressed against his own. He had shaken himself out of his fantasy and noticed his roommate looked a little lost, so we had cleared his throat to get the dude's attention before introducing himself. Three years later, his crush had only grown, but since Cas never seem to have any feelings for him, he never said anything.</p><p>     Dean finally got with the program and quickly borrowed some lotion from one of the girls across the hall and then made his way back to his dorm room, trying to psych himself up for the massage you promised. He walked back in the room and locked the door behind him, before turning and taking in the sight in front of him. Skin. Miles of tan, gorgeous skin. Cas lay on his bed shirtless, just like Dean had asked, and his toned back and arms were on naked display. Dean might have drooled a bit, sue him. He walked over to the bed with lotion in hand and that's when he ran into a bit of a problem. How the hell was he supposed to get in a good position to do this? FUCK! Fuck, Fuck, Fuck.</p><p>     “Cas, uh…is it all right if… um I…uh kind of straddle your legs? You know to like… uh, be able to reach your back easier?” He stammered, thankful that Cas was face down so that he couldn't see the blush that Dean felt growing on his face.</p><p>     “Sure.” His roommate replied, not bothering to look up.</p><p>     “Okay… good… okay.” Dean muttered as he swung his leg over the back of Cas’s thighs to get in position. He really Fucking hoped he didn't pop a boner and make this even more awkward. He squeezed some lotion into his hands and rubbed them together to warm it up. He held his breath as he reached over to place his hands on the wide shoulders in front of him. The first contact felt like a shock that lit his whole body up. He slowly let out of shaking breath as he dug his palms into the knotted deltoids of Cas’s back. He began to recall what he learned so he could put it into practice as he started to massage the man beneath him. He let himself relax into it. He could hear Cas’ breathing pick up, and the little grunts he let out at a few of the particularly deep passes of Dean's hands. Dean lean back down further to massage a knot on Cas’ shoulders, causing him to accidentally brush his cock against the swell of Cas’s ass, making him realize he had started to chub up at some point during the massage. He abruptly pulled back causing him to brush against Cas’ ass again and he heard Cas let out a moan below him. Dean froze, not sure what he should do.</p><p> </p><p>******************************************************************************************</p><p> </p><p>     Fuck. Cas had finally started to relax into the massage, after holding his breath for the first few minutes. It ended up being surprisingly easy to let go and forget his Crush, as he felt the knots being worked out of his muscles. He figured it would be easy to get through it then, without any embarrassment. Of course, his luck wasn't that good though. When Dean leaned over him and Cas felt the other man's cock press against his ass, he accidentally let a moan slip out, too relaxed to stop it in time. He felt Dean freeze up on top of him, and Cas held his breath, waiting to see what would happen. After the silence continued to draw out, Cas tried to think of any way he could fix it, blurting out the first thing he could think of.</p><p>     “Is…uh…is everything okay back there?” He asked stupidly, ears turning red.</p><p>     “Yep. Yep...uh…all good. Just stretching my hands, a bit. Starting to cramp up ya know.” He could hear Dean chuckle uncomfortably.</p><p>     “You can stop if you want.” Cas replied, giving Dean an out.</p><p>     “Nah. I'm good now. Just…uh, just lay there while I finish.” He felt Dean’s strong hands touch his back again. He tried to relax back into it, but he felt like a live wire. Every touch sent jolts of arousal to his cock, that was growing uncomfortably hard beneath him. He tried to stay still, he really did, but his cock was so hard he just wanted to ease some of the pressure on it. He shifted up slightly, causing him to brush his ass against Dean’s cock again, which he noticed was definitely not soft. <em>Huh</em>. He also thought he heard Dean whisper the word “Fuck”, but he wasn't sure. It piqued his curiosity though. Was Dean turned on? Was he attracted to Castiel too? His mind was going crazy just thinking about it. He had to know. He shifted again. more deliberately this time, to grind his ass up against Dean. He was rewarded with a much louder “Fuck” this time and Dean's hands grabbed Cas’ shoulders tightly. Cas decided to try and push his luck, needing to see where this could go. He pushed his ass out a bit harder, and let his hips roll into a dirty grind, which he repeated quickly. He didn't hold back any sounds and let out a moan when his cock rub against the bed below him, the friction feeling delicious. He felt Dean tense, and his breath hitch at the contact, before he bent down to whisper and Cas’ ear.</p><p>     “You're doing this on purpose, aren’t you?” Dean growled; arousal clear in his husky voice.</p><p>     “That depends.” Cas whispered back.</p><p>     “Depends on what?” Dean's hot breath tickled Cas’ ear.</p><p>     “On whether or not you want this, too.” Cas admitted, unsurely. Dean grinded his hard cock down on Cas’ ass.</p><p>     “That answer your question?” He could hear Dean's smirk in his voice.</p><p>     “Fuck.” Cas choked out.</p><p>     “Is that what you want Cas? Want me to Fuck you?” He taunted.</p><p>     “God yes!” Cas whimpered, too turned on to care how needy he sounded. Dean just chuckled as he sat up and pulled his own shirt over his head, before working on his pants. It was awkward, and there was some fumbling as they both struggled to get out of their respective pants with Dean not moving from on top of Cas. He felt Dean lean over to pull a bottle of lube out of his nightstand drawer, along with a condom.</p><p>     “Do you want the prep yourself, or do you want me to do it?” Dean him.</p><p>     “Neither actually. I.um…I don't like prep to be honest. Fingers just feel uncomfortable to me. Just use plenty of lube and go slow and I should be fine.” Cas told him.</p><p>     “You sure you don't want to be stretched Cas?” Dean asked un-convinced.</p><p>     “Yes, I'm sure. I know it's not the norm, but it's my preference.” He grumbled. It wasn't the first time someone didn't believe him that he really didn't like being fingered, and that he preferred no prep.</p><p>     “Okay. Just let me know if I hurt you okay?” He could hear the concern in Dean’s voice and it made him smile.</p><p>     “I Trust You Dean.”</p><p>     Dean leaned down and kissed Cas’ cheek, before sitting back up. Cas heard the cap of the lube flick open as Dean poured some on his cock before using his fingers to spread a healthy amount between Cas’ cheeks. He wiped his hands on the sheet and positioned the head of his cock at Cas's hole. Cas felt the pressure as the blunt head of Dean's cock began pushing in. When it breached the tight ring of muscle, Cas couldn't hold back a hiss at the stretch. Luckily Dean held still, giving Cas time to get used to it. After a few minutes, once Cas untensed, Dean pushed in another inch before stopping again to let Cas’ adjust. He pulled back and thrust in shallowly, taking his time to work his decently-sized cock into Cas’s tight hole. Finally, Dean pushed the last inch in, and his hips were flush against Cas’ ass. They both let out the breath they were holding, and groaned at the feeling; Dean at the hot, tight feeling wrapped around his cock, and Cas at the full feeling in the stretched ass.</p><p>     “Fuck Cas, so tight.” Dean moaned, breathing heavy above Cas.</p><p>     “God Dean, you feel huge. Fuck! I'm…I'm so full.” Cas choked out. “Move Dean!” he begged. Dean gently pulled out and thrust back in causing Cas to gasp. Two more thrust had him nailing Cas’s prostate, making him scream out in pleasure</p><p>     “Ah Fuck!” he yelled “Right there, Dean!”</p><p> </p><p>*************************************************************************************</p><p> </p><p>     Dean draped himself over Cas, as he reached underneath the other man's arms to grab his shoulders so we had more leverage to fuck down into him. He was able to hit Cas’ prostate on every thrust now. Over and over he Fucked down, making Cas call out each time.</p><p>     “Harder! <em>Please</em>” The man below him begged and Dean complied. He gripped Cas’s shoulders hard and Fucked him even harder. His orgasm was quickly approaching, but he held back wanting Cas to come first. He didn’t have to wait long.</p><p>     “Fuck Dean! I'm going to come!” The other men yelled out, just as Dean felt Cas’s ass clench tight around his cock, Cas moaning through his orgasm. A half-dozen thrusts later, Dean followed Cas over the edge as he filled the condom with his release. He took a minute to catch his breath before pulling out and tying off the condom, throwing it towards the wastebasket next to the bed. He collapsed down on his back next to Cas, breath still heavy. He turned his head and his eyes met Cas’. They both shared a small smile, before Dean pulled Cas close so the other man was laying on Deans chest and in his arms. Dean ran a soothing hand down Cas’ sweaty back, as he basked in the afterglow of a spectacular orgasm.</p><p>     “Dean?” he heard Cas whisper, voice sounding unsure.</p><p>     “What's Up Cas?”</p><p>     “Was that um…was that a one-time thing?” He asked shyly.</p><p>     “That depends” Dean answered.</p><p>     “Depends on what?” Cas asked.</p><p>     “On whether or not you want this, too.” Dean answered with a smirk. Cas chuckled and leaned up to look Dean in the eye before capturing his lips and heated kiss. Once Cas finally pulled back, he smirked back.</p><p>     “That answer your question?” He asked with a quirked eyebrow. Dean barked out a laugh at the role reversal, then kissed Cas again. They sank into the kiss for a few minutes until Dean broke it off to look at Cas. He cupped his cheek and smiled at the other man</p><p>     “Cas. Castiel… pretty sure I've been in love with you for three years.” He admitted. He heard Cas’ breath hitch.</p><p>     “Thought I was the only one.” Cas whispered back. “I love you too Dean. I have pretty much since I met you.” He revealed, eyes misted over.</p><p>     “Well then, want to be my boyfriend?” Dean asked cheekily, trying lighten the mood. He was rewarded with that gummy smile he fell in love with.</p><p>     “I'd love nothing more.” Cas replied as he leaned in to kiss Dean, smiles on both their faces.</p>
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